Water → HCID 25138432, compound

HRID 1044446Notes

Reaction equation

HRID 1044446 reaction equation
[CH2:1]([O:8][C:9]1[CH:32]=[C:31]([O:33]COC)[CH:30]=[CH:29][C:10]=1[C:11]1[CH2:12][O:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:15]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[CH2:1]([O:8][C:9]1[CH:32]=[C:31]([OH:33])[CH:30]=[CH:29][C:10]=1[C:11]1[CH2:12][O:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:15]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 80811Triphenylphosphonium bromideHCID 25138431HCID 25138431, compound

Product 1

HCID 25138432HCID 25138432, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2′,7-dibenzyloxy-4′-methoxymethyloxy-isoflav-3-ene (0.480 g, 1 mmol) in acetonitrile:water (20 mL:1 mL) was added triphenyl phosphine hydrobromide (0.788 g, 2 mmol). The reaction was heated to 50° C. for ca. 2 hrs. After disappearance of the starting material (TLC), the solvent was evaporated at 20° C. The residue was extracted with EtOAc:water (3×10 mL:10 mL). The organic layers were combined, dried and evaporated. The residue was chromatographed over silica using hexanes:EtOAc (5:1). The organic fractions were evaporated to provide 0.374 g (78%) of product as an oil. Because of the instability of this intermediate, it was immediately used for the next step: TLC Rf0.43, in hexanes:EtOAc (5:1); 1H NMR (600 MHz, DMSO-d6) δ 9.66 (s, 1H, OH), 7.46-7.32 (m, 10H, 2×CH5), 7.14, 7.13 (d, 1H, J=8.4 Hz, Ar—H5), 7.01-6.99 (d, 1H, J=7.8 Hz, Ar—H6′) 6.57-6.55 (m, 2H, H4/Ar—H5′), 6.59-6.52 (d, 1H, J=2.4 Hz, Ar—H8), 6.48-6.47 (d, 1H, J=2.4 Hz, Ar—H3′), 6.41-6.39 (dd, 1H, 2J=8.4 Hz, 3J=2.4 Hz, Ar—H5′), 5.07 (s, 4H, PhCH2), 4.85 (s, 2H, H2).

Workup

  1. customAfter disappearance of the starting material (TLC), the solvent was evaporated at 20° C
  2. extractionThe residue was extracted with EtOAc
  3. customdried
  4. customevaporated
  5. customThe residue was chromatographed over silica
  6. customThe organic fractions were evaporated

Sources & evidence

ORD record
ord-fe1ff4d9e1474c9daa27b2b8d74c694f
Source dataset
uspto-grants-2013_10
Patent number
US08563599B2

Reaction notes

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